Potassium Hydroxide → HCID 86611483, compound

HRID 452526Notes

Reaction equation

HRID 452526 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].CO[C:8](=[O:33])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:19][C:18]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)=[CH:11][C:10]=1[CH3:32]>CO>[Cl:30][C:28]1[CH:29]=[C:24]([C:18]2([C:20]([F:23])([F:21])[F:22])[O:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:2][OH:3])=[O:33])=[C:10]([CH3:32])[CH:11]=3)[CH2:19]2)[CH:25]=[C:26]([Cl:31])[CH:27]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59563501Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

Product 1

HCID 86611483HCID 86611483, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
40 °C

Procedure

In a solution of 0.30 g of hydroxylamine hydrochloride in 10 ml of methanol, a solution of 0.65 g of potassium hydroxide in 5 ml of methanol was added, then a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid methyl ester synthesized similarly to Steps 1 to 4 of Synthetic Example 28 in 10 ml of methanol was added, and stirred at 40° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1) was added in the residue, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. Toluene was added in the residue and the remaining acetic acid was distilled off azeotropically to to obtain 1.01 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid as white crystal.

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1)
  4. additionwas added in the residue
  5. extractionextracted with ethyl acetate (20 ml×2)
  6. dry with materialdried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  7. distillationthe solvent was distilled under reduced pressure
  8. additionToluene was added in the residue
  9. distillationthe remaining acetic acid was distilled off azeotropically

Sources & evidence

ORD record
ord-edf814666ad146e5bce43ddf3d48384a
Source dataset
uspto-grants-2013_07
Patent number
US08492311B2

Reaction notes

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